Molecules 2012, 17(10), 12102-12120; doi:10.3390/molecules171012102
Article

Acetylated and Methylated β-Cyclodextrins as Viable Soluble Supports for the Synthesis of Short 2′-Oligodeoxyribo-nucleotides in Solution

Received: 12 September 2012; in revised form: 12 October 2012 / Accepted: 12 October 2012 / Published: 16 October 2012
(This article belongs to the Special Issue Nucleic Acid Analogs)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: Novel soluble supports for oligonucleotide synthesis 11ac have been prepared by immobilizing a 5′-O-protected 3′-O-(hex-5-ynoyl)thymidine (6 or 7) to peracetylated or permethylated 6-deoxy-6-azido-β-cyclodextrins 10a or 10b by Cu(I)-promoted 1,3-dipolar cycloaddition. The applicability of the supports to oligonucleotide synthesis by the phosphoramidite strategy has been demonstrated by assembling a 3′-TTT-5′ trimer from commercially available 5′-O-(4,4′-dimethoxytrityl)thymidine 3′-phosphoramidite. To simplify the coupling cycle, the 5′-O-(4,4′-dimethoxytrityl) protecting group has been replaced with an acetal that upon acidolytic removal yields volatile products. For this purpose, 5′-O-(1-methoxy-1-methylethyl)-protected 3′-(2-cyanoethyl-N,N-diisopropyl-phosphoramidite)s of thymidine (5a), N4-benzoyl-2′-deoxycytidine (5b) and N6-benzoyl-2′-deoxyadenosine (5c) have been synthesized and utilized in synthesis of a pentameric oligonucleotide 3′-TTCAT-5′ on the permethylated cyclodextrin support 11c.
Keywords: cyclodextrin; oligonucleotides; phosphoramidites; soluble support; synthesis
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MDPI and ACS Style

Molina, A.G.; Kungurtsev, V.; Virta, P.; Lönnberg, H. Acetylated and Methylated β-Cyclodextrins as Viable Soluble Supports for the Synthesis of Short 2′-Oligodeoxyribo-nucleotides in Solution. Molecules 2012, 17, 12102-12120.

AMA Style

Molina AG, Kungurtsev V, Virta P, Lönnberg H. Acetylated and Methylated β-Cyclodextrins as Viable Soluble Supports for the Synthesis of Short 2′-Oligodeoxyribo-nucleotides in Solution. Molecules. 2012; 17(10):12102-12120.

Chicago/Turabian Style

Molina, Alejandro G.; Kungurtsev, Vyacheslav; Virta, Pasi; Lönnberg, Harri. 2012. "Acetylated and Methylated β-Cyclodextrins as Viable Soluble Supports for the Synthesis of Short 2′-Oligodeoxyribo-nucleotides in Solution." Molecules 17, no. 10: 12102-12120.

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